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Boston at a glance

Why visit Boston?

Boston is America’s heritage city, site of key events during the American Revolution, and it mixes gravitas with great walks, cheap eats and a vibrant nightlife. Plus, it’s the gateway to the leafy glories of New England.

Local hotspot

Gentrification has turned the formerly dodgy South End (not to be confused with South Boston) into one of the city’s most fashionable neighbourhoods, and among its stately Victorian terraces are plenty of cutting-edge galleries – head for the SoWa (‘South of Washington’) district – and some great eating, concentrated on and just off Tremont and Washington.

You probably didn’t know

That the Charlie Card, which is the rechargeable pre-pay card for bus and subway travel, gets its name from the 1949 ‘MTA Song’, which tells the tale of a man called Charlie trapped on the Boston subway system (then known as the Metropolitan Transit Authority system). It was a hit for the folk-singing Kingston Trio in 1959.

Suggested reading and viewing about Boston

Read Dennis Lehane’s Mystic River (2001), which was adapted for film and directed by Clint Eastwood – much of Lehane’s work features Boston; watch Martin Scorsese’s The Departed (2006), a Boston story that makes much use of local landmarks.

Boston facts

Population: 655,884 (2014)

Annual visitor numbers: 16 million (2014)

January mean temperature: -2°C

August mean temperature: 23°C

Things to do in Boston

The Paramount

For the best start to your day in Boston ever, hit the Paramount, a small café-diner on Charles Street, Beacon Hill, just north of the Common. From 7am on weekdays or 8am on weekends, it serves up massive plates of eggs (however you like ’em), waffles, pancakes and French toast. It’s open for lunch and dinner too, but you could definitely live off the breakfasts.

Neptune Oyster

If you want to get into an argument in Boston, steer the conversation to politics, sport or where to find the city’s best lobster roll. In the case of the latter, you can slam-dunk a winner by namechecking Neptune Oyster; here, it comes cold (with mayo) or hot (with butter – and better), served in a toasted brioche bun stuffed with tail, claw and knuckle. When you fly to Boston, try it at 63 Salem Street in North End.

Sam La Grassa’s

A Boston institution, Sam La Grassas’s is a stunning lunchtime-only deli serving landmark Reuben sandwiches (meaning they are so big you can see them for miles around), as well as all kinds of other cooked meats, salads and soups, including clam chowder. Find it on Province Street in the Financial District.

Sweet Cheeks

A beautiful southern-style BBQ joint right next to home of the Red Sox, Fenway Park, the cutely named Sweet Cheeks majors in smoked, slow-cooked meats, like brisket, ribs, chicken and pulled pork served in a sandwich, tray or heaped on paper by the pound. The meat comes with sides of everything from grits to coleslaw, and pickles. Hell, the place even does salads.

Neptune Oyster in Boston

Brendan Behan

It just isn’t possible to go to Boston and not visit an Irish pub. There’s no shortage from which to choose but we recommend hopping on the subway and heading out to the neighbourhood of Jamaica Plain to drop in on the Brendan Behan, a little dimly-lit den of drink-fuelled bonhomie. Note – while there’s plenty of choice of beer, there’s no food, but you’re allowed to bring your own from one of the many takeaways nearby.

The Delux

When you visit Boston, do a short walk from central Copley Square is the Delux. It’s small and narrow with pinewood-panelled walls, papered with album sleeves and old posters. It gave everyone a scare by briefly closing in 2014, but it reopened to retain the crown of Boston’s hippest bar. Settle into a leather booth or pull up a stool at the bar, but leave your cards at home because this place is cash only. Find it at 100 Chandler Street, South End.

Jacob Wirth

Founded in 1868 in Boston, German-American beer hall Jacob Wirth must be doing something right because almost a century-and-a-half later and it’s still rammed most nights. It could be the palpable sense of history, the 30-plus beers on draft, the Thursday and Friday-night piano-led sing-alongs or the dining specials (Monday’s is 45 cent wings, Tuesday’s is 25 cent hot dogs).

Bleacher Bar

If you don’t have tickets for a game in Boston but want to soak up some atmosphere (and some suds), the Bleacher Bar is actually tucked under the seating at baseball ground Fenway Park and has a view of the field. Be warned though, it gets packed on game days, and even on non-game days you have to put your name down in advance for a table with a view.

Bleacher Bar

South End

South End has become the place for vintage in Boston. Every Sunday it hosts the SoWa Vintage Market, with stalls covering fashion, furnishings, jewellery and arts. Just up the street is Bobby From Boston, with maybe the coolest selection of vintage menswear you’ll ever see (there are women’s items too). Farm & Fable specialises in vintage cookbooks and kitchenware, while SAULT New England sells an eclectic mix of vintage Americana with preppy brands of apparel and accessories.

Back Bay

Back Bay is the go-to neighbourhood for independent stores and boutique shopping, particularly Newbury Street. This is where you find the flagship store for Boston-grown lifestyle outfitters Life Is Good (283 Newbury Street), no less than three branches of 2nd Time Around (176, 219 and 324 Newbury Street), which has ever-changing designer stock at bargain prices, and the self-explanatory Trident Booksellers and Café (338 Newbury Street).

Beacon Hill

Beacon Hill is one of the Boston’s most historic and loveliest areas, and – if your credit card can bear it – Charles Street is a great place to shop. Start at Moxie (21 Charles Street) for designer shoes, bags and jewellery, then Dress (70 Charles Street) for, well, dresses by small-scale designers. At 88 Charles Street is the curiously named December Thieves, showcasing more unusual jewellery, handbags and accessories, and at 133 Charles Street is a shop called Good, which mixes Scandinavian-style homeware with unique gifts and jewellery.

SoWa Vintage Market in Boston's South End

The Isabella Stewart Gardner Museum

While the Museum of Fine Arts boasts a world-class collection from the pre-Columbian to the 20th century, if you only visit one art museum in Boston make it the Isabella Stewart Gardner Museum. It’s not just the 2,000 priceless objects on display but the Venetian-style palazzo in which they are housed, with a four-storey greenhouse courtyard that’s the equal of any artwork.

The Isabella Stewart Gardner Museum in Boston

The Freedom Trail

Boston is a great city for walking, and why not learn as you go by following the Freedom Trail, a 2.5-mile route around the city that traces the events leading up to and following the American War of Independence, highlighting the key role the city played. You can do it with a guide or on your own by following the markers set into the pavement.

The Sinclair & Wally’s Cafe

Boston is one of America’s great music cities, with a raft of great venues attracting the biggest names. But, if you just want somewhere you can roll up, grab a beer and a bite and enjoy the band, check out the Sinclair over in Cambridge. It holds an intimate 525 people, and it’s run by The Bowery Presents, the New York-based company behind the legendary Bowery Ballroom. For jazz, head to Wally’s Cafe, the oldest continually operating jazz club in the US, with music 365 days a year.